WO1998009616A1 - Feste geschäumte wirkstoffzubereitungen - Google Patents
Feste geschäumte wirkstoffzubereitungen Download PDFInfo
- Publication number
- WO1998009616A1 WO1998009616A1 PCT/EP1997/004550 EP9704550W WO9809616A1 WO 1998009616 A1 WO1998009616 A1 WO 1998009616A1 EP 9704550 W EP9704550 W EP 9704550W WO 9809616 A1 WO9809616 A1 WO 9809616A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- active ingredient
- ingredient forms
- active
- melt
- blowing agent
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
- A61K31/612—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid
- A61K31/616—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid by carboxylic acids, e.g. acetylsalicylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/401—Proline; Derivatives thereof, e.g. captopril
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4422—1,4-Dihydropyridines, e.g. nifedipine, nicardipine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
- A61K9/122—Foams; Dry foams
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/122—Hydrogen, oxygen, CO2, nitrogen or noble gases
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2339/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
- C08J2339/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C08J2339/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
Definitions
- the present invention relates to solid, partially or completely foamed active ingredient forms based on thermoplastically processable polymers.
- the invention further relates to methods for producing such active ingredient forms.
- foamed plastics can be produced by extrusion of melts containing volatile blowing agents.
- Rapidly releasing dosage forms are generally achieved by rapidly disintegrating the dosage form through the use of insoluble but swellable disintegrants.
- Rapid release can also be achieved with pharmaceutical forms obtained by the melt extrusion process by using relatively low molecular weight, water-soluble thermoplastic polymers as matrix polymers.
- the disadvantage of this, however, is that when such polymers are used, they often have problems relating to the storage stability of the finished pharmaceutical forms.
- the solid, foamed active substance preparations according to the invention can contain, as active substances, all substances which can be incorporated into the polymer melt without decomposing under the processing conditions.
- Suitable active ingredients are, for example:
- Vitamins can also be formulated according to the invention. These include the vitamins of the A group and the B group, whereby in addition to Bl, B2, B6 and B12 as well as nicotinic acid and N cot amide
- Compounds with vitamin B properties are understood, such as. B. Aden, Chol, pantothenic acid, Biot, adenyl acid, folic acid, orotic acid, pangamic acid, carnite, p-ammobenzoic acid, myo-ionic and lipoic acid. Furthermore vitamins of the C group, D group, E group, F group, H group, I and J group, K group and P group.
- Very particularly preferred active ingredients according to the invention are ibuprofen, acetylsalicylic acid, paracetamol, phenazone, flurbifrofen, captopril, nifedipm, acetyl system, naftidrofuryl, verapamil and furosemide.
- Plant protection agents other biocides or veterinary substances are also suitable as active ingredients.
- thermoplastic polymers come into consideration as thermoplastically processable polymers for the polymer matrix.
- Particularly suitable polymers are water-soluble, thermoplastically processable homo- or copolymers of N-Vmylpyrrolidons or mixtures of such polymers.
- the polymers usually have glass transition temperatures in the range from 80 to 190, preferably 90 to 175 ° C.
- Suitable homopolymers are, for example, polymers with K values according to Fikent ⁇ cher in the range from 10 to 30.
- Suitable copolymers can be, as comonomers, unsaturated carboxylic acids, for example methacrylic acid, crotonic acid, maleic acid, itaconic acid, and their esters with alcohols having 1 to 12, preferably 1 to 8, carbon atoms , furthermore hydroxyethyl or hydroxypropyl acrylate and ethacrylate, (meth) acrylic acid, the anhydrides and half esters of maleic and itaconic acid (the half ester preferably only after the polymer sation is formed ) , or Vmylmonomere such as N-Vmylcaprolactam, Vmylacetat, Vmylbutyrat and Vmylpropionat, contain or also mixtures of the mentioned comonomers.
- unsaturated carboxylic acids for example methacrylic acid, crotonic acid, maleic acid, itaconic acid, and their esters with alcohols having 1 to 12, preferably 1 to 8, carbon atoms , furthermore hydroxyethyl
- Preferred comonomers are acrylic acid and, particularly preferably, vinyl acetate.
- the comonomers can be present in amounts of 20 to 70% by weight.
- Copolymers which are obtained from 60% by weight N-vinylpyrrolidone and 40% by weight vinyl acetate are very particularly preferred according to the invention.
- Suitable polymers are, for example, homopolymers or copolymers of vinyl chloride, polyvinyl alcohols, polystyrene, polyrates,
- the active substance preparations can also contain starches, degraded starches, casein, pectin, chitin, chitosan, gelatin or shellac as matrix components, which can be processed in the melt with the addition of conventional plasticizers.
- fillers e.g. the oxides of magnesium, aluminum, silicon and titanium as well as lactose, mannitol, sorbitol, xylitol, pentaerythritol and its derivatives, the amount of filler being approx. 0.02 to 50, preferably 0.2 to 20% by weight. % lies.
- Flow regulators which may be mentioned are, for example, the mono-, di- and tri-glycerides of the long-chain fatty acids such as C 12 -, C ⁇ 4 -, Ci 6 ⁇ and cis-fatty acid, waxes such as carnauba wax and lecithme, the amount being approx. 1 to 30, preferably 0.1 to 5 wt .-% is.
- plasticizers include, for example, polyhydric alcohols such as propylene glycol, glycerin, pentaerythritol and sorbitol as well as sodium diethylsulfosuccinate, mono-, di- and triacetate of glycerol and polyethylene glycol ester.
- the amount of plasticizer is about 0.5 to 15, preferably 0.5 to 5 wt .-%.
- lubricants which may be mentioned are stearates of aluminum or calcium, as well as talc and silicones, their amount being about 0.1 to 5, preferably 0.1 to 3,% by weight.
- Stabilizers which may be mentioned are, for example, light stabilizers, antioxidants, radical scavengers and stabilizers against microbial attack, the amount of which is preferably from about 0.01 to 0.05% by weight.
- the active ingredient component can either be mixed beforehand with the polymer and then extruded, or metered in during the extrusion of the blowing agent-containing polymer melt.
- the quantitative ratios of the individual components in the preparation can be varied within wide limits. Depending on the effective dose and the release rate of the active ingredient, the amount thereof can be 0.1 to 90% by weight of the active ingredient preparation. The amount of the polymer can be 10 to 99.9% by weight. In addition, 0 to 50% by weight of one or more auxiliary substances can be present.
- Fully foamed active substance preparations according to the invention are preferably produced by extrusion of a melt which, in addition to one or more active substances, contains one or more thermoplastically processable polymers and, if appropriate, customary auxiliaries, the melt being impregnated with volatile, physiologically acceptable blowing agents.
- Suitable volatile, physiologically acceptable blowing agents are gaseous blowing agents such as carbon dioxide, nitrogen, air, noble gases such as helium or argon, chlorofluorocarbons or nitrous oxide (laughing gas), carbon dioxide and / or nitrogen being preferred.
- the melt is preferably produced in the extruder, particularly preferably in a twin-screw extruder.
- the mixing of the active ingredient (s) with the polymers and, if appropriate, further additives can be carried out before or after the melting of the polymers by the processes customary in the art. In the case of temperature-sensitive active substances in particular, it is advisable to add them only after the thermoplastic has melted.
- the melt can be obtained at temperatures from 50 to 200, preferably 100 to 180 ° C., the suitable temperature being based primarily on the glass transition temperature of the polymer or polymers. Usually, the polymers will melt at temperatures above their glass transition temperature.
- the impregnation of the melt with the blowing agent is preferably carried out at pressures of 10 to 300 bar, particularly preferably 50 to 200 bar. Under these conditions, between 1 and 15% by weight of the blowing agent dissolves in the melt.
- the melt containing blowing agent is preferably cooled to temperatures which are in the range from 0 to 50 ° C. above the glass transition temperature of the blowing agent-free polymer or polymer mixture.
- the process according to the invention can be carried out in a single extruder with different temperature zones.
- a tandem extrusion system consisting of two extruders coupled to one another is preferred, the first extruder, in which the melting of the polymer and the blowing agent loading of the melt takes place, is preferably a twin-screw extruder with good mixing action, and the second extruder is a single-screw extruder with low shear action and high cooling capacity .
- the still plastic strand emerging from the extruder nozzle expands to a foam under the normal pressure present outside the extruder.
- the degree of foaming of the active ingredient preparation can be controlled via the amount of blowing agent added and the extrusion temperature. A high degree of foaming results in a lower density and thus a high dissolution rate of the active ingredient form. If higher densities are desired, a high blowing agent content which is favorable for the preparation can be reduced by degassing directly to the nozzle gap to such an extent that only a slightly foamed product is obtained.
- the foamed active ingredient preparation then becomes the respective the desired active ingredient forms are deformed, for example by pelleting, granulation or tableting according to known processes.
- the solid, fully foamed active substance preparations usually have densities in the range from 200 to 1000 g / 1, preferably 200 to 800 g / 1.
- Another embodiment of the method according to the invention relates to the production of multi-layer partially or completely foamed active substance-containing forms by coextrusion. At least two masses, each containing at least one of the thermoplastic binders mentioned, at least one of which contains an active ingredient and at least one of which is impregnated with a gaseous, physiologically unimportant blowing agent in the manner already described, are co-extruded and then into or the desired dosage form deformed.
- the mass is prepared separately for each layer of the active ingredient.
- the respective starting components are processed in a separate extruder under the conditions already described for the above process variant to form active substance-old melts. You can work for each layer under optimal material-specific conditions. For example, a different processing temperature can be selected for each layer.
- the respective masses can, for example, also be impregnated with different amounts of blowing agent, so that layers with different foaming levels are produced.
- the molten or plastic masses from the individual extruders are filled, shaped and discharged into a common coextrusion tool.
- the shape of the co-extrusion tools depends on the shape of the active substance desired. For example, tools with a flat exit gap, so-called wide-slot tools, and tools with a circular gap-shaped exit cross section are suitable.
- the nozzle design is based on the polymeric binder used and the desired shape.
- the desired active ingredient form or pharmaceutical form is shaped.
- a variety of shapes can be created depending on the coextrusion tool and the type of molding.
- a strand that emerges from a wide-slot tool and that has in particular two or three layers can be punched or cut eg with glow wire, produce open multilayer tablets.
- open multilayer tablets can be separated using a tool with an outlet cross-section in the form of a circular gap by hot cutting, ie by cutting or chopping the strand immediately after it emerges from the nozzle, or preferably by cold cutting, ie by cutting or chopping the strand after at least partial cooling become.
- Closed active ingredient forms i.e. Forms in which the active substance-containing layer is completely surrounded by an active substance-free layer can be obtained in particular by means of a tool with an outlet cross-section in the form of a circular gap by treating the support in a suitable squeezing device, as shown, for example, in FIGS. 1 and 2, in the examples below is explained, is shown. It is advantageous if the outer layer of the multilayer tablet, when the outer layer has already cooled, is still plastically deformable when it enters the squeezing device. In this way, tablets in particular, preferably oblong tablets, dragees, pastilles and pellets, can be produced.
- foamed active substance-containing molds can be produced by extruding a melt which, in addition to one or more active substances, comprises at least one thermoplastic binder, subjecting the still plastic melt to a shaping and then the solid active substance-containing form under pressure impregnated with one of the above-mentioned gaseous blowing agents, for example a conventional autoclave at pressures in the range of
- the impregnated form expands to a partially or completely foamed form.
- the degree of foaming depends on the duration of the diagnosis process and can be set as desired.
- This process variant is preferably suitable for the production of partially foamed molds which have an outer foamed shell and a non-foamed core and thus have a step-shaped release profile.
- the foamed molds can also be provided with a conventional active substance-permeable coating, so that floating floating molds can be obtained in a simple manner.
- floating forms can be used for pharmaceutical purposes or also for veterinary or agricultural products, for example for the production of slowly sinking fish food.
- the active compound erf dungsgehold obtained solid, foamed - ukache 5 Z, the dispersed homogeneously the active substance contained in the poly- meric matrix, dissolve very rapidly and thus permit rapid release of the active ingredient.
- Advertising Z ukache a simple and economic way sheep Liche receive 10 the - through the process erfmdungsgeofficee the foamed active ingredient can. It is also advantageous that the viscosity-reducing action of the blowing agent allows extrusion at significantly lower temperatures than without blowing agent, so that the active substances are subjected to less thermal stress.
- Copolymers of 60% by weight N-vinylpyrrolidone and 40% by weight vinyl acetate with a K value of 30 were melted and extruded at 150 ° C. in a twin-screw extruder.
- the still thermoplastic strand was after that described in EPA 240 906
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK97944775T DK0932393T3 (da) | 1996-09-03 | 1997-08-21 | Faste opskummede sammensætninger af aktive stoffer |
BR9711982A BR9711982A (pt) | 1996-09-03 | 1997-08-21 | Forma de ingrediente ativo e processos para produzir a mesma |
JP10512176A JP2000517327A (ja) | 1996-09-03 | 1997-08-21 | 固体の発泡作用物質調合物 |
AU46177/97A AU740856B2 (en) | 1996-09-03 | 1997-08-21 | Solid foamed active substance preparations |
DE59706898T DE59706898D1 (de) | 1996-09-03 | 1997-08-21 | Feste geschäumte wirkstoffzubereitungen |
AT97944775T ATE215362T1 (de) | 1996-09-03 | 1997-08-21 | Feste geschäumte wirkstoffzubereitungen |
CA002264588A CA2264588C (en) | 1996-09-03 | 1997-08-21 | Solid foamed active substance preparations |
US09/254,012 US6150424A (en) | 1996-09-03 | 1997-08-21 | Solid foamed active substance preparations |
IL12843997A IL128439A (en) | 1996-09-03 | 1997-08-21 | Solid foamed active ingredient preparations and processes for producing such preparations |
EP97944775A EP0932393B1 (de) | 1996-09-03 | 1997-08-21 | Feste geschäumte wirkstoffzubereitungen |
BG103214A BG103214A (en) | 1996-09-03 | 1999-02-26 | Solid foam-forming active substance containing preparation |
NO991011A NO991011L (no) | 1996-09-03 | 1999-03-02 | Fast skumpreparater med aktiv bestandel og fremgangsmÕte for fremstilling derav |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19635676.8 | 1996-09-03 | ||
DE19635676A DE19635676A1 (de) | 1996-09-03 | 1996-09-03 | Feste geschäumte Wirkstoffzubereitungen |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998009616A1 true WO1998009616A1 (de) | 1998-03-12 |
Family
ID=7804471
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1997/004550 WO1998009616A1 (de) | 1996-09-03 | 1997-08-21 | Feste geschäumte wirkstoffzubereitungen |
Country Status (22)
Country | Link |
---|---|
US (1) | US6150424A (zh) |
EP (1) | EP0932393B1 (zh) |
JP (1) | JP2000517327A (zh) |
CN (1) | CN1124129C (zh) |
AT (1) | ATE215362T1 (zh) |
AU (1) | AU740856B2 (zh) |
BG (1) | BG103214A (zh) |
BR (1) | BR9711982A (zh) |
CA (1) | CA2264588C (zh) |
CZ (1) | CZ67699A3 (zh) |
DE (2) | DE19635676A1 (zh) |
DK (1) | DK0932393T3 (zh) |
ES (1) | ES2175469T3 (zh) |
HR (1) | HRP970472A2 (zh) |
HU (1) | HUP9904101A3 (zh) |
IL (1) | IL128439A (zh) |
NO (1) | NO991011L (zh) |
PT (1) | PT932393E (zh) |
RU (1) | RU2200004C2 (zh) |
TR (1) | TR199900447T2 (zh) |
WO (1) | WO1998009616A1 (zh) |
ZA (1) | ZA977861B (zh) |
Cited By (5)
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WO2004084936A3 (en) * | 2003-02-06 | 2005-06-16 | Cerus Corp | Modified free-living microbes, vaccine compositions and methods of use thereof |
WO2006131570A2 (fr) * | 2005-06-10 | 2006-12-14 | Armines | Procede de fabrication d'un materiau composite comprenant une substance active |
US7691393B2 (en) | 2003-02-06 | 2010-04-06 | Anza Therapeutics, Inc. | Listeria attenuated for entry into non-phagocytic cells, vaccines comprising the Listeria, and methods of use thereof |
US7927606B2 (en) | 2003-02-06 | 2011-04-19 | Aduro Biotech | Modified free-living microbes, vaccine compositions and methods of use thereof |
US8636929B2 (en) | 2010-05-21 | 2014-01-28 | Basf Se | Nanoporous foamed active compound-containing preparations based on pharmaceutically acceptable thermoplastically workable polymers |
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DE19733505A1 (de) * | 1997-08-01 | 1999-02-04 | Knoll Ag | Schnell wirksames Analgeticum |
DE19900457A1 (de) * | 1999-01-08 | 2000-07-13 | Basf Ag | Verfahren zur Herstellung von festen Dosierungsformen |
US6733789B1 (en) | 1999-01-21 | 2004-05-11 | Biovail Laboratories, Inc. | Multiparticulate bisoprolol formulation |
EP1175205B1 (en) | 1999-11-12 | 2006-06-14 | Abbott Laboratories | Solid dispersion comprising ritonavir, fenofibrate or griseofulvin |
US7364752B1 (en) | 1999-11-12 | 2008-04-29 | Abbott Laboratories | Solid dispersion pharamaceutical formulations |
US20040185099A1 (en) * | 2000-01-20 | 2004-09-23 | Biovail Laboratories, Inc. | Multiparticulate bisoprolol formulation |
DE10026698A1 (de) | 2000-05-30 | 2001-12-06 | Basf Ag | Selbstemulgierende Wirkstoffformulierung und Verwendung dieser Formulierung |
DE10032456A1 (de) | 2000-07-04 | 2002-01-31 | Lohmann Therapie Syst Lts | Schnell zerfallende Darreichungsform zur Freisetzung von Wirkstoffen im Mundraum oder in Körperhöhlen |
US6555581B1 (en) | 2001-02-15 | 2003-04-29 | Jones Pharma, Inc. | Levothyroxine compositions and methods |
GB0113841D0 (en) * | 2001-06-07 | 2001-08-01 | Boots Co Plc | Therapeutic agents |
US20030198671A1 (en) * | 2001-08-10 | 2003-10-23 | Franz G. Andrew | Levothyroxine compositions having unique plasma AUC properties |
US20030165564A1 (en) * | 2001-10-29 | 2003-09-04 | Franz G. Andrew | Levothyroxine compositions having unique triiodothyronine Tmax properties |
US20030118652A1 (en) * | 2001-11-15 | 2003-06-26 | John Kelly | Methods and compositions for use of (S)-bisoprolol |
US20030091633A1 (en) * | 2001-11-15 | 2003-05-15 | John Kelly | Methods and compositions for use of (S)-bisoprolol |
AU2003206382B2 (en) * | 2002-01-03 | 2008-01-24 | Smithkline Beecham Corporation | Novel pharmaceutical dosage forms and method for producing same |
DE10207394B4 (de) * | 2002-02-21 | 2007-03-29 | Lts Lohmann Therapie-Systeme Ag | Geschmacksmaskierte oblatenförmige Arzneizubereitung |
US20030235613A1 (en) * | 2002-06-19 | 2003-12-25 | Cts Chemical Industries Ltd. | Popping oral administration form |
DE10227607A1 (de) * | 2002-06-20 | 2004-01-08 | Boxler Gmbh & Co. Kg | Paneel-Verbindung |
US8802139B2 (en) | 2003-06-26 | 2014-08-12 | Intellipharmaceutics Corp. | Proton pump-inhibitor-containing capsules which comprise subunits differently structured for a delayed release of the active ingredient |
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- 1997-08-21 PT PT97944775T patent/PT932393E/pt unknown
- 1997-08-21 WO PCT/EP1997/004550 patent/WO1998009616A1/de active IP Right Grant
- 1997-08-21 DE DE59706898T patent/DE59706898D1/de not_active Expired - Lifetime
- 1997-08-21 AT AT97944775T patent/ATE215362T1/de not_active IP Right Cessation
- 1997-08-21 CA CA002264588A patent/CA2264588C/en not_active Expired - Lifetime
- 1997-08-21 HU HU9904101A patent/HUP9904101A3/hu unknown
- 1997-08-21 ES ES97944775T patent/ES2175469T3/es not_active Expired - Lifetime
- 1997-08-21 EP EP97944775A patent/EP0932393B1/de not_active Expired - Lifetime
- 1997-08-21 CN CN97199572A patent/CN1124129C/zh not_active Expired - Lifetime
- 1997-08-21 TR TR1999/00447T patent/TR199900447T2/xx unknown
- 1997-08-21 RU RU99107556/14A patent/RU2200004C2/ru active
- 1997-08-21 US US09/254,012 patent/US6150424A/en not_active Expired - Lifetime
- 1997-08-21 IL IL12843997A patent/IL128439A/xx not_active IP Right Cessation
- 1997-08-21 DK DK97944775T patent/DK0932393T3/da active
- 1997-08-21 AU AU46177/97A patent/AU740856B2/en not_active Ceased
- 1997-08-21 JP JP10512176A patent/JP2000517327A/ja active Pending
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Cited By (8)
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WO2004084936A3 (en) * | 2003-02-06 | 2005-06-16 | Cerus Corp | Modified free-living microbes, vaccine compositions and methods of use thereof |
US7691393B2 (en) | 2003-02-06 | 2010-04-06 | Anza Therapeutics, Inc. | Listeria attenuated for entry into non-phagocytic cells, vaccines comprising the Listeria, and methods of use thereof |
US7833775B2 (en) | 2003-02-06 | 2010-11-16 | Aduro Biotech | Modified free-living microbes, vaccine compositions and methods of use thereof |
US7927606B2 (en) | 2003-02-06 | 2011-04-19 | Aduro Biotech | Modified free-living microbes, vaccine compositions and methods of use thereof |
WO2006131570A2 (fr) * | 2005-06-10 | 2006-12-14 | Armines | Procede de fabrication d'un materiau composite comprenant une substance active |
FR2886938A1 (fr) * | 2005-06-10 | 2006-12-15 | Armines Ass Loi De 1901 | Procede d'extrusion permettant de fabriquer des dispersions solides de principes actifs pharmaceutiques dans une matrice polymere |
WO2006131570A3 (fr) * | 2005-06-10 | 2007-06-07 | Armines | Procede de fabrication d'un materiau composite comprenant une substance active |
US8636929B2 (en) | 2010-05-21 | 2014-01-28 | Basf Se | Nanoporous foamed active compound-containing preparations based on pharmaceutically acceptable thermoplastically workable polymers |
Also Published As
Publication number | Publication date |
---|---|
ZA977861B (en) | 1999-03-02 |
JP2000517327A (ja) | 2000-12-26 |
TR199900447T2 (xx) | 1999-05-21 |
CA2264588C (en) | 2005-10-18 |
IL128439A (en) | 2003-02-12 |
RU2200004C2 (ru) | 2003-03-10 |
CA2264588A1 (en) | 1998-03-12 |
DE59706898D1 (de) | 2002-05-08 |
PT932393E (pt) | 2002-09-30 |
CN1124129C (zh) | 2003-10-15 |
DK0932393T3 (da) | 2002-07-01 |
BR9711982A (pt) | 1999-08-24 |
ATE215362T1 (de) | 2002-04-15 |
IL128439A0 (en) | 2000-01-31 |
EP0932393A1 (de) | 1999-08-04 |
NO991011L (no) | 1999-03-03 |
US6150424A (en) | 2000-11-21 |
BG103214A (en) | 1999-09-30 |
CN1237103A (zh) | 1999-12-01 |
HUP9904101A2 (hu) | 2000-04-28 |
HRP970472A2 (en) | 1998-08-31 |
CZ67699A3 (cs) | 1999-05-12 |
AU4617797A (en) | 1998-03-26 |
ES2175469T3 (es) | 2002-11-16 |
HUP9904101A3 (en) | 2001-11-28 |
DE19635676A1 (de) | 1998-03-05 |
AU740856B2 (en) | 2001-11-15 |
NO991011D0 (no) | 1999-03-02 |
EP0932393B1 (de) | 2002-04-03 |
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